


the who, the what,  the why, the how

by isloremipsumafterall



Category: Supergirl (TV 2015)
Genre: Alternate Universe - No Powers, M/M
Language: English
Status: Completed
Published: 2017-02-22
Updated: 2017-02-22
Packaged: 2018-09-26 07:05:42
Rating: General Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 1,135
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/9872768
Author URL: https://archiveofourown.org/users/isloremipsumafterall/pseuds/isloremipsumafterall
Summary: In which Winn is dared by Kara to ask out the next person who walks through the door and that just so happens to be James Olsen.





	

**Author's Note:**

  * For [plinys](https://archiveofourown.org/users/plinys/gifts).



> Jess and I agreed to a fic swap last month and I got a little lazy in finishing while she did wonderfully in hers so here's to Jess. Hope it's okay.

Winn regretted even agreeing to it. He and Kara played these sorts of games in college all the time – after a few beers- but playing it now in the small diner next to CatCo seemed like a bad idea. Kara had pouted though, claiming boredom, and he’d caved.

 

“Any random person?” Winn asked, his eyes darting around the dinner. It was filled with people from work but there were also some strangers he didn’t recognize.

 

Kara nodded absently, eying her milkshake like she was trying to figure out if there was a secret to the bottom of the cup that offered more.

 

The bell jingled with a sign that someone had come in and Winn tapped his fingers on the table in nervous energy. Reasonably, he and Kara would be leaving soon so he could ask this new stranger and then flee before anyone from work even saw him embarrass himself. On the other hand, Winn’s mouth felt dry as he looked at the stranger, a handsome man who was taller than Winn and fiddling with the strap of his messenger bag.

 

Before Winn could talk himself out of it he stood up, drawing Kara’s attention and she glanced around to see who he was thinking of asking. He made himself walk to the door and smiled widely at the man, “Hi there,” He winced internally, had his voice just cracked? “Uh, so I know I’m just leaving and you’re just getting in but maybe later the two of us could sit down…together… or something.” Kara’s babbling was clearly spreading, or that’s what he liked to pretend it was.

 

The man if anything looked amused, a slow smile dawning on his lips, “Do I get a name first?”

 

“Oh, right, I’m Winn.” He stuck his hand out out of habit and nearly jumped when the other man shook it.

 

“James. And sure, the food here good enough to eat for dinner too?”

 

Winn gaped, “Uh, yeah, food’s…food. I mean, it’s great.” He could hear Kara snicker behind him and vowed revenge.

 

“So see you at six then?” James continued and Winn stared at him.

 

“You’re saying yes?” He blurted out.

 

James’ eyebrows shot up, “Something wrong with that?”

 

“What? No. No no no, I just mean, I didn’t expect that.” Winn shot a panicked glance at Kara who was watching them curiously now.

 

“I don’t see why not.” James grinned and shrugged, “Unless you’re luring me into a trap.”

 

“I can’t tell if that was a Star Wars joke or not.” Winn admitted, “But also, no, no trap.”

 

“Then I think we’re good.” James’ hand landed on Winn’s shoulder, squeezed it lightly and then let go. He turned to walk away and Kara came up behind him with his bag.

 

“We should go,” Kara whispered, “Before you start the freak out.”

 

As Kara was dragging him out the door he could still hear himself saying, “He said yes?” He turned to her as soon as they were through the door, “What am I supposed to do now?”

 

Kara smiled at him warily, “Go on a date?”

 

“What have I done?” Winn groaned and Kara pushed him along back to CatCo, patting his shoulder in sympathy the whole time.

 

~~

 

Work was dragging when they got back in, for once no one was even having tech issues leaving Winn to play around with code that wasn’t for work. Normally he’d enjoy that time but he kept thinking back to the date he’d agreed to with James.

 

“Winn,” Kara’s voice came from above him and made him jump, “Staff meeting, remember?”

 

Winn made a face, “She doesn’t even know I have a name, why do I have to go?” He asked rhetorically as he followed Kara into the meeting and then froze on the spot when he saw James was standing next to Cat’s desk.

 

“Um,” He began with nothing else really to say and when Cat raised an eyebrow at him he shut his mouth and stepped to the side so other people could enter the room. He caught Kara’s eye while she was looking between him and James in panic and just shrugged back in equal confusion.

 

“…introduce our new staff editor and photographer, James Olsen.” He heard Cat the last bit of what Cat said. “Now our articles have been lacking lately.” Cat continued onwards and Winn phased her out again.

 

James noticed his staring and flashed him an easy grin, like it was no big deal the random guy who had asked him out an hour ago was now his coworker. He bounced on his feet, waiting for the meeting to end so he could go back to his desk and panic in peace but when Cat excused them – more kicked them out – he was stopped by a hand on his arm right before he got to his desk.

 

“Hey, so,” James cleared his throat and it was nice to see he wasn’t sure about this too, “I didn’t realize you worked here.”

 

“Tech support.” Winn blurted out, “That’s me, good old…tech support. I didn’t know you were going to be here either. This is weird, is this weird?”

 

James shrugged, “A little. But uh, it doesn’t mean we still can’t go out tonight. If you’re still up for it.”

 

Winn opened his mouth and then shut it with a click and luckily Kara intervened before he made an ass of himself somehow.

 

“He’d love to.” Kara put a hand on his shoulder. “Right Winn?” She shot him a glance and edged her head towards James, a quiet indicator that he was being weird by not saying anything while James was waiting for an answer.

 

“Right.” Winn nodded far too quickly, “I mean, we’re coworkers, that’s cool. We can still date.”

 

“I think it gives us more of a chance to get to know each other.” James admitted and Kara snuck away from them. James was smiling again and it was really distracting how attractive he looked when he did that which was personally unfair for Winn.

 

“Great.” Winn agreed though he wasn’t really paying attention.

 

“So,” James began, “I need help setting up my computer.”

 

“I’m your man.” Winn said and then made a face, “Uh, IT guy that is.” James had pressed him lips together so he didn’t laugh but Winn could tell he wanted to. “Okay, haha.” Winn crossed his arms. “I know how that sounded.”

 

James clapped him on the shoulder and pressed his hand down to steer Winn towards his new office. “I didn’t think it sounded that bad.”

 

Winn let out a strangled noise that he’d deny later. He’d also deny that he kept sneaking looks at James all day even when he was questioned about it by James later on their date(s, plural.)


End file.
